A New Kind of Sexy: Fashion with Jennifer Westfeldt

The actress-writer-producer-director dresses to impress and chats about her career and love life

by Margot Dougherty

Photograph: Todd Cole

Jennifer Westfeldt was a New York theater actress when she went to Los Angeles in 1997 to visit a friend. Within a week she’d landed a sitcom—Two Guys, a Girl and a Pizza Place, which co-starred Ryan Reynolds—and met a little-known actor named Jon Hamm, whom she soon started dating.

Things seem to fall into place around Westfeldt, who is still with Hamm. Before Two Guys started filming, a night of sketches she put on with actress Heather Juergensen was optioned by a Hollywood studio. It eventually became 2001’s Kissing Jessica Stein, the sleeper indie hit about two straight women so disillusioned with the men they meet that they fall for each other instead. Westfeldt cowrote, coproduced and costarred. “I’m a doer,” she says.

Apparently. She has since written, produced and starred in two more films, 2006’s Ira & Abby and last year’s Friends with Kids. She also directed Friends, which centers on best pals (Westfeldt and Adam Scott of Parks and Recreation) who hope to avoid the relationship pitfalls of their married friends with children by having a baby together without becoming romantically involved. (Hamm coproduced and had a role as the nasty husband of Kristen Wiig’s character.)

Westfeldt spent two years bringing the movie to the screen, doing everything from casting to raising money to dealing with frozen camera lenses that had to be thawed with hair dryers. “Every day there is something cataclysmic,” she says of indie filming. “You can’t believe you don’t just have a heart attack and drop dead.

“I don’t consider myself a writer,” Westfeldt adds, evidence notwithstanding. “I’m really an actress. But three times I’ve been moved enough by what I see in my peer group to want to document it.”

The comic anguish of her scripts hardly reflects her own experience. “I’ve been a serial monogamist since the age of 12,” she says. “An eight-year relationship ended in my mid-twenties, and then I met Jon. I thrive in a relationship. It’s my state of being. I don’t really get it any other way.” Yet she and Hamm, who split their time between New York and L.A., are in no rush to marry. “We’re both children of divorce,” she says, “so it’s never struck us as the great solution.”